Selective synthesis and reactivity expansion of α,β-unsaturated geminal diazides,Organic Chemistry Frontiers

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Selective synthesis and reactivity expansion of α,β-unsaturated geminal diazides
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2022-03-08 , DOI: 10.1039/d2qo00008c
Chen Chen ₁ , Jun Ge ₁ , Ling He ₁

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α,β-Unsaturated gem-diazides were selectively obtained catalyzed by Yb(TfO)₃ using α,β-unsaturated aldehydes as substrates and TMSN₃ as a nitrogen source under mild and simple conditions in moderate yields without Schmidt rearrangement and allylic rearrangement. The study on the reactivity and application expansion of α,β-unsaturated gem-diazides demonstrated the access to α,β-unsaturated bistriazole, monotriazole, and macrocycle precursors, bis(heterocyclyl)methylene derivatives and imine derivatives with strong electron-withdrawing groups under simple conditions. Compound 9c exhibited antiproliferative activity against A549 which could be a lead compound for the discovery of anticancer agents.

中文翻译：

α,β-不饱和偕二叠氮化物的选择性合成及反应性扩展

Yb(TfO) 3_以α,β-不饱和醛为底物，TMSN ₃为氮源，在温和、简单的条件下，不发生施密特重排和烯丙基重排，选择性获得α,β-不饱和偕二叠氮化合物，产率适中。对α,β-不饱和偕二叠氮化合物的反应性和应用扩展研究表明，在α,β-不饱和双三唑、单三唑和大环前体、双（杂环基）亚甲基衍生物和亚胺衍生物下具有强吸电子基团简单的条件。化合物9c对 A549 表现出抗增殖活性，这可能是发现抗癌剂的先导化合物。

更新日期：2022-03-08

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